TY - JOUR
T1 - Total synthesis of kingianinsA, D, and F
AU - Drew, Samuel L.
AU - Lawrence, Andrew L.
AU - Sherburn, Michael S.
PY - 2013/4/8
Y1 - 2013/4/8
N2 - A synthesis fit for a king: The total synthesis of (±)-kingianinsA, D, and F has been achieved in ten steps. Key features include the gram-scale synthesis and partial reduction of a conjugated tetrayne to a (Z,Z,Z,Z)-tetraene, the domino 8π-6π electrocyclic ring closure of a (Z,Z,Z,Z)-tetraene, and the radical-cation-catalyzed formal Diels-Alder dimerization of functionalized bicyclo[4.2.0]octadiene precursors.
AB - A synthesis fit for a king: The total synthesis of (±)-kingianinsA, D, and F has been achieved in ten steps. Key features include the gram-scale synthesis and partial reduction of a conjugated tetrayne to a (Z,Z,Z,Z)-tetraene, the domino 8π-6π electrocyclic ring closure of a (Z,Z,Z,Z)-tetraene, and the radical-cation-catalyzed formal Diels-Alder dimerization of functionalized bicyclo[4.2.0]octadiene precursors.
KW - biomimetic synthesis
KW - domino reactions
KW - natural products
KW - polyynes
KW - radical cations
UR - http://www.scopus.com/inward/record.url?scp=84875866470&partnerID=8YFLogxK
U2 - 10.1002/anie.201210084
DO - 10.1002/anie.201210084
M3 - Article
SN - 1433-7851
VL - 52
SP - 4221
EP - 4224
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 15
ER -